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2,5-Hexanediol

Chemical compound From Wikipedia, the free encyclopedia

2,5-Hexanediol is an organic compound with the formula CH3CH(OH)CH2CH2CH(OH)CH3. It is both a glycol and a secondary alcohol.[1] It is a colorless water-soluble viscous liquid.[2][3][4] The chemical properties are well understood and have been extensively reported and studied.[5] It has the IUPAC name of hexane-2,5-diol[6] and the CAS Registry Number CAS 2935-44-6.[7]

Quick facts Names, Identifiers ...
2,5-Hexanediol
Names
Preferred IUPAC name
Hexane-2,5-diol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.019.010 Edit this at Wikidata
EC Number
  • 220-910-3
  • InChI=1S/C6H14O2/c1-5(7)3-4-6(2)8/h5-8H,3-4H2,1-2H3
    Key: OHMBHFSEKCCCBW-UHFFFAOYSA-N
  • CC(CCC(C)O)O
Properties
C6H14O2
Molar mass 118.176 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H315, H319, H335
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Other names

  • (2R,5R)-2,5-hexanediol
  • 2,5-Dihydroxyhexane
  • Diisopropanol
  • Hexan-2,5-diol
  • [R-(R*,R*)]-2,5-hexanediol
  • hexane-2,5-diol

Manufacture

One common method of manufacture of the compound is from yeast.[8] Another method involves the reduction of acetonylacetone.[9] The material has two chiral carbons and thus has a number of enantiomers. Processes have been researched and developed to produce enantiopure products and by a continuous process.[10][11] Some synthesis has been carried out from keto hexanoates.[12]

Uses

One of the uses of the material is to synthesize polyesters.[13] and also fine chemicals.[14]

Toxicity

The toxicity of the material has been studied and is reasonably well understood.[15][16][17][18] It can affect the eyes and has some neurotoxic effects.[19]

References

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